The Bard on Board: Many actors and directors have noticed a connection between Drowsy and Shakespeare's As You Like It: Four weddings, main couple falls in and out of love, girl pretends to be something she isn't, last marriage comes out of nowhere, priest for the wedding comes down from the sky...
Big Lipped Alligator Moment: The Man puts in the wrong record, and we get to hear "Message From a Nightingale", which has absolutely nothing to do with the plot.
Crowning Moment of Funny: The opening monologue, the spit-take scene, "Bride's Lament", literally every scene in which the Chaperone or Aldolpho appear, 95% of Man In Chair's comments, the record skipping at the end of "Toledo Surprise", the gangsters' puns, "Message From A Nightingale"...it's a cliche to end entries like this with "let's just say the whole show", but The Drowsy Chaperone has earned it.
Those puns are heinous. Even my crush on the gangsters isn't enough to squash how horrible those puns are. The rest of it though...YES!